Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations

Bew, Sean P. ORCID: https://orcid.org/0000-0002-9087-9463, El-Taeb, Gamila M. M., Jones, Simon, Knight, David W. and Tan, Wen-Fei (2007) Expedient syntheses of β-iodofurans by 5-endo-dig cyclisations. European Journal of Organic Chemistry, 2007 (34). pp. 5759-5770. ISSN 1434-193X

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Abstract

5-endo-dig cyclisations of 3-alkyne-1,2-diols using iodine as the electrophile proceed smoothly to deliver excellent yields of the corresponding β-iodofurans. The necessary precursors are available from a number of different approaches, notably regioselective bis-hydroxylation of conjugated enynes and the addition of acetylides to α-hydroxy carbonyl groups. The initial iodofurans can be homologated using a number of strategies, ranging from various transition metal-catalysed couplings to halogen-metal exchange and subsequent coupling with an electrophile. Hence, this method overall represents a flexible, relatively brief and very efficient approach to a variety of highly substituted furans. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Item Type:	Article
Faculty \ School:	Faculty of Science > School of Chemistry (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Synthetic Chemistry (former - to 2017) Faculty of Science > Research Groups > Chemistry of Materials and Catalysis
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	Rachel Smith
Date Deposited:	20 Apr 2011 09:08
Last Modified:	24 Sep 2024 09:38
URI:	https://ueaeprints.uea.ac.uk/id/eprint/29668
DOI:	10.1002/ejoc.200700681

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